Talbutal

Identification

Generic Name

Talbutal

DrugBank Accession Number

DB00306

Background

Talbutal, also called 5-allyl-5-sec-butylbarbituric acid, is a barbiturate with a short to intermediate duration of action. Talbutal is a schedule III drug in the U.S.

Type

Small Molecule

Groups

Approved, Illicit

Structure

Similar Structures

Weight: Average: 224.2563
Monoisotopic: 224.116092388
Chemical Formula: C₁₁H₁₆N₂O₃

Synonyms

(RS)-5-allyl-5-sec-butylpyrimidine-2,4,6(1H,3H,5H)-trione
5-allyl-5-sec-butylbarbituric acid
sec-Butyl allyl barbituric acid
Talbutal
Talbutale
Talbutalum

External IDs

HSDB 3397
WIN 5095

Pharmacology

Indication

For use as a sedative and hypnotic.

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Drug Discovery

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Contraindications & Blackbox Warnings

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Pharmacodynamics

Talbutal is a short to intermediate-acting barbiturate that is a nonselective central nervous system (CNS) depressant. As with other barbiturates, talbutal is capable of producing all levels of CNS mood alteration from excitation to mild sedation, hypnosis, and deep coma. Barbiturates may also induce anesthesia at sufficiently high therapeutic doses.

Mechanism of action

Talbutal binds to GABA_A receptors at a distinct binding site associated with a Cl^- ionopore of the receptor. Upon binding, talbutal increases the duration of time for which the Cl^- ionopore is open, leading to prolonged inhibitory effect of GABA at the postsynaptic thalamic neuron.

Target	Actions	Organism
AGamma-aminobutyric acid receptor subunit alpha-1	potentiator	Humans
AGamma-aminobutyric acid receptor subunit alpha-2	potentiator	Humans
AGamma-aminobutyric acid receptor subunit alpha-3	potentiator	Humans
AGamma-aminobutyric acid receptor subunit alpha-4	potentiator	Humans
AGamma-aminobutyric acid receptor subunit alpha-5	potentiator	Humans
AGamma-aminobutyric acid receptor subunit alpha-6	potentiator	Humans
UNeuronal acetylcholine receptor subunit alpha-4	antagonist	Humans
UNeuronal acetylcholine receptor subunit alpha-7	antagonist	Humans
UGlutamate receptor 2	antagonist	Humans
UGlutamate receptor ionotropic, kainate 2	antagonist	Humans
AGABA(A) Receptor	positive allosteric modulator	Humans

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects

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Toxicity

Acute barbiturate poisoning is associated with symptoms such as drowsiness, confusion, coma, respiratory depression, hypotension, and shock.

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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1,2-Benzodiazepine	The risk or severity of adverse effects can be increased when Talbutal is combined with 1,2-Benzodiazepine.
Acetazolamide	The risk or severity of adverse effects can be increased when Talbutal is combined with Acetazolamide.
Acetophenazine	The risk or severity of adverse effects can be increased when Talbutal is combined with Acetophenazine.
Aclidinium	Talbutal may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
Agomelatine	The risk or severity of adverse effects can be increased when Talbutal is combined with Agomelatine.
Alfentanil	The risk or severity of adverse effects can be increased when Talbutal is combined with Alfentanil.
Alimemazine	The risk or severity of adverse effects can be increased when Talbutal is combined with Alimemazine.
Alloin	The therapeutic efficacy of Alloin can be decreased when used in combination with Talbutal.
Almotriptan	The risk or severity of adverse effects can be increased when Talbutal is combined with Almotriptan.
Alosetron	The risk or severity of adverse effects can be increased when Talbutal is combined with Alosetron.

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Food Interactions

Not Available

Products

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International/Other Brands: Lotusate (Sanofi Aventis)

Chemical Identifiers

UNII: 4YIR8202AX
CAS number: 115-44-6
InChI Key: BJVVMKUXKQHWJK-UHFFFAOYSA-N
InChI: InChI=1S/C11H16N2O3/c1-4-6-11(7(3)5-2)8(14)12-10(16)13-9(11)15/h4,7H,1,5-6H2,2-3H3,(H2,12,13,14,15,16)
IUPAC Name: 5-(butan-2-yl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
SMILES: CCC(C)C1(CC=C)C(=O)NC(=O)NC1=O

References

General References

Not Available

External Links

KEGG Drug: D06887
PubChem Compound: 8275
PubChem Substance: 46507821
ChemSpider: 7976
RxNav: 89810
ChEBI: 134923
ChEMBL: CHEMBL1200802
Therapeutic Targets Database: DAP000670
PharmGKB: PA164779051
Wikipedia: Talbutal

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count

Pharmacoeconomics

Manufacturers

Sanofi aventis us llc

Packagers

Not Available

Dosage Forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	109 °C	PhysProp
water solubility	1810 mg/L at 25 °C	MEYLAN,WM et al. (1996)
logP	1.47	HANSCH,C ET AL. (1995)
pKa	7.79 (at 25 °C)	KORTUM,G ET AL (1961)

Predicted Properties

Property	Value	Source
Water Solubility	2.46 mg/mL	ALOGPS
logP	1.87	ALOGPS
logP	1.59	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	8.48	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.27 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	58.05 m³·mol^-1	ChemAxon
Polarizability	22.48 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9272
Blood Brain Barrier	+	0.984
Caco-2 permeable	-	0.5931
P-glycoprotein substrate	Substrate	0.6383
P-glycoprotein inhibitor I	Non-inhibitor	0.5341
P-glycoprotein inhibitor II	Non-inhibitor	0.9761
Renal organic cation transporter	Non-inhibitor	0.9352
CYP450 2C9 substrate	Non-substrate	0.7904
CYP450 2D6 substrate	Non-substrate	0.9009
CYP450 3A4 substrate	Non-substrate	0.7245
CYP450 1A2 substrate	Non-inhibitor	0.8455
CYP450 2C9 inhibitor	Non-inhibitor	0.8308
CYP450 2D6 inhibitor	Non-inhibitor	0.9229
CYP450 2C19 inhibitor	Non-inhibitor	0.7692
CYP450 3A4 inhibitor	Non-inhibitor	0.8764
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9375
Ames test	Non AMES toxic	0.6105
Carcinogenicity	Non-carcinogens	0.8617
Biodegradation	Not ready biodegradable	0.9918
Rat acute toxicity	3.5595 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9879
hERG inhibition (predictor II)	Non-inhibitor	0.9537

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
GC-MS Spectrum - EI-B	GC-MS	splash10-00kf-9400000000-724aeaec6df65c3e5931
GC-MS Spectrum - CI-B	GC-MS	splash10-004i-0090000000-603a585be8f03eb2145e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Targets

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Details1. Gamma-aminobutyric acid receptor subunit alpha-1

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Potentiator

General Function: Inhibitory extracellular ligand-gated ion channel activity
Specific Function: Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Gene Name: GABRA1
Uniprot ID: P14867
Uniprot Name: Gamma-aminobutyric acid receptor subunit alpha-1
Molecular Weight: 51801.395 Da

References

Whiting PJ: The GABAA receptor gene family: new opportunities for drug development. Curr Opin Drug Discov Devel. 2003 Sep;6(5):648-57. [Article]
Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]
Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]
Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Details2. Gamma-aminobutyric acid receptor subunit alpha-2

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Potentiator

General Function: Inhibitory extracellular ligand-gated ion channel activity
Specific Function: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name: GABRA2
Uniprot ID: P47869
Uniprot Name: Gamma-aminobutyric acid receptor subunit alpha-2
Molecular Weight: 51325.85 Da

References

Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]

Details3. Gamma-aminobutyric acid receptor subunit alpha-3

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Potentiator

General Function: Inhibitory extracellular ligand-gated ion channel activity
Specific Function: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name: GABRA3
Uniprot ID: P34903
Uniprot Name: Gamma-aminobutyric acid receptor subunit alpha-3
Molecular Weight: 55164.055 Da

References

Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]

Details4. Gamma-aminobutyric acid receptor subunit alpha-4

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Potentiator

General Function: Inhibitory extracellular ligand-gated ion channel activity
Specific Function: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name: GABRA4
Uniprot ID: P48169
Uniprot Name: Gamma-aminobutyric acid receptor subunit alpha-4
Molecular Weight: 61622.645 Da

References

Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]

Details5. Gamma-aminobutyric acid receptor subunit alpha-5

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Potentiator

General Function: Transporter activity
Specific Function: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name: GABRA5
Uniprot ID: P31644
Uniprot Name: Gamma-aminobutyric acid receptor subunit alpha-5
Molecular Weight: 52145.645 Da

References

Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]

Details6. Gamma-aminobutyric acid receptor subunit alpha-6

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Potentiator

General Function: Inhibitory extracellular ligand-gated ion channel activity
Specific Function: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name: GABRA6
Uniprot ID: Q16445
Uniprot Name: Gamma-aminobutyric acid receptor subunit alpha-6
Molecular Weight: 51023.69 Da

References

Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]
Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]

Details7. Neuronal acetylcholine receptor subunit alpha-4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General Function: Ligand-gated ion channel activity
Specific Function: After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeabl...
Gene Name: CHRNA4
Uniprot ID: P43681
Uniprot Name: Neuronal acetylcholine receptor subunit alpha-4
Molecular Weight: 69956.47 Da

References

Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
Arias HR, Bhumireddy P: Anesthetics as chemical tools to study the structure and function of nicotinic acetylcholine receptors. Curr Protein Pept Sci. 2005 Oct;6(5):451-72. [Article]
Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]

Details8. Neuronal acetylcholine receptor subunit alpha-7

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General Function: Toxic substance binding
Specific Function: After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The cha...
Gene Name: CHRNA7
Uniprot ID: P36544
Uniprot Name: Neuronal acetylcholine receptor subunit alpha-7
Molecular Weight: 56448.925 Da

References

Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
Arias HR, Bhumireddy P: Anesthetics as chemical tools to study the structure and function of nicotinic acetylcholine receptors. Curr Protein Pept Sci. 2005 Oct;6(5):451-72. [Article]
Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]

Details9. Glutamate receptor 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General Function: Ionotropic glutamate receptor activity
Specific Function: Receptor for glutamate that functions as ligand-gated ion channel in the central nervous system and plays an important role in excitatory synaptic transmission. L-glutamate acts as an excitatory ne...
Gene Name: GRIA2
Uniprot ID: P42262
Uniprot Name: Glutamate receptor 2
Molecular Weight: 98820.32 Da

References

Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]

Details10. Glutamate receptor ionotropic, kainate 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General Function: Kainate selective glutamate receptor activity
Specific Function: Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L-glutamate induces a co...
Gene Name: GRIK2
Uniprot ID: Q13002
Uniprot Name: Glutamate receptor ionotropic, kainate 2
Molecular Weight: 102582.475 Da

References

Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]

Details11. GABA(A) Receptor (Protein Group)

Kind: Protein group
Organism: Humans
Pharmacological action: Yes
Actions: Positive allosteric modulator

General Function: Inhibitory extracellular ligand-gated ion channel activity
Specific Function: Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...

Components:

Name	UniProt ID
Gamma-aminobutyric acid receptor subunit alpha-1	P14867
Gamma-aminobutyric acid receptor subunit alpha-2	P47869
Gamma-aminobutyric acid receptor subunit alpha-3	P34903
Gamma-aminobutyric acid receptor subunit alpha-4	P48169
Gamma-aminobutyric acid receptor subunit alpha-5	P31644
Gamma-aminobutyric acid receptor subunit alpha-6	Q16445
Gamma-aminobutyric acid receptor subunit beta-1	P18505
Gamma-aminobutyric acid receptor subunit beta-2	P47870
Gamma-aminobutyric acid receptor subunit beta-3	P28472
Gamma-aminobutyric acid receptor subunit delta	O14764
Gamma-aminobutyric acid receptor subunit epsilon	P78334
Gamma-aminobutyric acid receptor subunit gamma-1	Q8N1C3
Gamma-aminobutyric acid receptor subunit gamma-2	P18507
Gamma-aminobutyric acid receptor subunit gamma-3	Q99928
Gamma-aminobutyric acid receptor subunit pi	O00591
Gamma-aminobutyric acid receptor subunit theta	Q9UN88

References

ChEMBL Compound Report Card [Link]

Drug created on June 13, 2005 13:24 / Updated on July 03, 2021 09:02

Talbutal

Identification

Structure for Talbutal (DB00306)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Targets

References

References

References

References

References

References

References

References

References

References

Components:

References